Water → HCID 69213515, compound

HRID 2375759Notes

Reaction equation

HRID 2375759 reaction equation
[H-].[Na+].[NH:3]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].Cl[CH2:19][C:20]1[CH:21]=[C:22]([S:26][CH2:27][C:28]([OH:30])=[O:29])[CH:23]=[CH:24][CH:25]=1.O.[CH3:32]N(C)C=O>>[CH3:32][O:30][C:28](=[O:29])[CH2:27][S:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][N:3]([C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:21]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 279800Di-tert-butyl IminodicarboxylateHCID 69213296HCID 69213296, compound

Product 1

HCID 69213515HCID 69213515, compound

Conditions

Temperature
60 °C

Procedure

44 mg (1.1 mmol) of a 60% dispersion of sodium hydride in oil are suspended in 8 ml of dimethylformamide (DMF), and 238 mg (1.1 mmol) of di-t-butyl iminodicarboxylate are added. The reaction mixture is stirred at 60° C. for 30 min and then cooled to room temperature. A solution of 230 mg (1 mmol) of the methyl ester of [3-(chloromethyl)phenylthio]acetic acid in 3 ml of DMF is then added. The reaction medium is stirred at 50° C. for 90 min and then cooled and poured into 30 ml of water. The aqueous phase obtained is extracted with ethyl acetate (twice) and the combined organic phases are dried over sodium sulfate and concentrated under reduced pressure. The crude product is purified by chromatography on silica gel using a toluene/ethyl acetate mixture (95/5; v/v) as the eluent to give 300 mg of the expected compound in the form of a colorless oil (yield=73%).

Workup

  1. temperaturecooled to room temperature
  2. stirringThe reaction medium is stirred at 50° C. for 90 min
  3. temperaturecooled
  4. customThe aqueous phase obtained
  5. extractionis extracted with ethyl acetate (twice) and the combined organic phases
  6. dry with materialare dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product is purified by chromatography on silica gel using a toluene/ethyl acetate mixture (95/5; v/v) as the eluent

Sources & evidence

ORD record
ord-6dc4dc181b3d40499108ed789a0a08be
Source dataset
uspto-grants-2008_12
Patent number
US07465811B2

Reaction notes

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